


Two Brothers And A Sister

by PrincessOfErebor



Series: Two Brothers And A Sister [1]
Category: Supernatural
Genre: Angst, Demon!Dean, F/M, Gen, Sister!winchester
Language: English
Status: Completed
Published: 2019-01-21
Updated: 2019-02-20
Packaged: 2019-10-09 00:34:54
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 7
Words: 4,879
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17396744
Author URL: https://archiveofourown.org/users/PrincessOfErebor/pseuds/PrincessOfErebor
Summary: Olivia Winchester shows up in town. This is her story.





	1. Chapter 1

Sam was furious. Dean had disappeared, nowhere to be found. As it turns out, Crowley turned Dean into a demon.The last thing he needed was a distraction.

Trying to find a cure was hard enough, but the knock at the bunker door irritated Sam something awful. Dean wasn’t there to order pizza. There were no hunter buddies nearby. He growled as he approached the door. 

When he opened the door, two shy brown eyes looked up at him. “Hi I’m Olivia. Um...is Dean here?”

“Do I know you?” He asked, suddenly feeling suspicious as he crossed his arms.

She stepped back feeling a little hurt. She said with tears in her eyes, “I’m your sister…”

~ ~ ~

While Olivia made herself at home in one of the guest rooms, Sam had a rather heated conversation with Cas.

“I have a sister?!”, he fumed and grimaced, “It’s bad enough that my brother is running around doing who knows what and I don’t need some random girl showing up claiming to be my sister.”

Cas calmly stated, “There does seem to be something different about her from what you’ve told me. She doesn’t show any ill will; and as far as I know, none of my brothers or sisters need a vessel like Adam.”

Sam huffed and sat down at the table running his hand through his hair. “Even if she is legit, how do I even tell her that Dean is a demon?”

~ ~ ~

“A...a demon..?” Olivia gulped. “Like...the whole black eyes and evil tendencies kind of demon? I mean...I believe in that sort of thing but I didn’t think I’d get so up close and personal with it.” She laughed nervously.

Cas leaned over and whispered to Sam, “Should I show her?”

Before Sam could respond, Olivia overheard it and asked, “Show me what?”

Cas quietly stood a few feet from the table. The lights went off and on as Olivia saw the outline of two black raven-like wings protruding from his back. 

“Yep that’s definitely up close and personal…” She tapped her fingers on the table.

Sam seemed to soften towards her a little. They’d been fooled in the past by so-called genuine people but there was something different about Olivia. She almost had the same personality as Adam, but a little more shut off and laid back. Maybe Cas was right.

She spoke up after the awkward silence. “So...if Dean is a demon then how…?”

Sam seemed to read her thoughts. “How do we get him back?”

She nodded and he explained, “Well we don’t really know what to do, but if we can get him back to the bunker and trap him in the dungeon, we have more of a chance of figuring it out.”

Olivia understood a little. She came to bunker expecting to introduce herself to the Winchester brothers, but instead, she was on a mission to help Sam rescue one.


	2. Two Brothers And A Sister - Chapter 2

**Summary for the Chapter:**

> Olivia Winchester is the newest addition to the Winchester family. Will she and Sam warm up to each other?

The last thing on Olivia’s mind was sleep. Tossing and turning in her bed, all she kept thinking about was the confused expression on Sam’s face when she broke the news. She didn’t mean to drop that kind of bomb on him, but how could she possibly have known about the whole demon thing? 

Olivia finally gave up on the notion of sleep and decided to explore the bunker. No harm in that right? She pulled her black cardigan around her shoulders and slowly peeked out her bedroom door, almost as if she was expecting something evil to turn that corner. A chill ran down her spine as her steps echoed along the hallway. Suddenly she paused; she wasn’t alone. There were other footsteps accompanying hers. Fight or flight? Flight was her first instinct but the paranormal enthusiast in her really wanted to investigate. 

She turned around to face whatever it was head-on. The sheer suspense of the moment was enough to make her heart race. The footsteps came closer and closer, but she couldn’t see through the darkness of the hall. Now would be a good time to run she thought to herself. But before she could make any movement, she saw the outline of a tall man approaching her. This is it...this is how I’m gonna die. A demon. All sorts of things were running through her mind. 

All Olivia could do was squeak, “Please don’t hurt me”.

In return, a sleepy voice replied, “Um...I’m not? I’m just going to the kitchen.”

Olivia breathed a sigh of relief. The voice was familiar; it was only Sam. “Geez man you scared the bajeebas out of me. I couldn’t sleep…”

Both of them stood there awkwardly glancing at each other. Olivia’s random appearance at the bunker was nothing short of inconvenient and both of them knew it. 

Sam sighed, “Honestly me either…hey um, maybe you could help after all. Come with me.”

She followed him to the library and soaked in the warm, dim lights. Sitting next to Sam, she observed as he grew tense as he watched footage from what looked like a security camera from a grocery store. He formed a fist and winced as a man looked straight up at the camera and...holy crap his eyes turned black. Olivia jumped back and cowered. 

“Is that…?” She couldn’t even finish her question but Sam did.

“Yep that’s Dean. And we have got to find him before he causes any more trouble”, he continued, “I was hoping you could tag along and help me. It’d be a good time to get to know you.”

Olivia tilted her head and had a thoughtful moment. Sam was softening up towards her; maybe this wasn’t such a bad idea after all. “Yea, I’d like that.”  
Eventually, the two of them tracked down Dean’s latest location. He had been at a bar, and according to the bouncer, Dean started a fight. The bouncer looked pretty banged up himself. 

Sam thanked the man and handed him a phone number. “Thanks. If you have anymore information please let me know.”

As the bouncer walked away, Olivia huffed. “How are we going to find Dean? This is getting ridiculous.”

The night was long and sleepless for Olivia; she was so worried that she’d never find her eldest brother. There was little consolation in some of the things they’d researched. She finally closed her eyes hoping and praying things would turn out okay.


	3. Two Brothers And A Sister - Chapter 3

**Summary for the Chapter:**

> Sam finally finds out where Dean has been hiding out. He also has to make a tough decision; will Olivia accompany him or not?

The next morning, Olivia woke up but was hesitant to open her eyes. She was hoping all of this had been some weird random dream. But unfortunately it wasn’t; Sam’s ruffling around for his clothes ruined the moment. She pulled the pillow over her head to block the sunlight but Sam wouldn’t have it.

“No ma’am. We’ve got a long day ahead of us remember?”, he said sternly. His brows creased when there was no answer from her. “Seriously Olivia, if you want to help, you’ve got to cooperate with me.”

Her only response was a growl but she crawled out of the bed. “Can I at least have some coffee?”

“Yep I already poured it up for you”, he pointed towards the general direction of the motel’s coffee pot. 

While Olivia was busy packing her things in the Impala, Sam heard a familiar posh voice behind him. His shoulders instinctively tensed up, knowing that the owner of the voice had to be up to no good.

“Hello Bullwinkle”, was the greeting. 

Sam turned and attempted to be friendly, but it was really difficult. Facing the very being that turned his brother into a demon in the first place was enough to make any man angry. He gritted his teeth. “Hello Crowley. What do you want?”

“I want your brother out of my hair. He’s currently wreaking havoc at a nearby bar.” It seemed Crowley was ready to rid himself of the monster he’d created.

Olivia returned and crossed her arms when she saw Crowley. “Who’s this Sam?”

Crowley merely bowed sarcastically. “King of hell, at your service.”

“King...of what now?”, Olivia was thoroughly confused. She was totally fine with the whole demon conundrum but did she seriously just hear him say king of hell?

“You heard me...king of hell. And who might you be?” He responded with a mischievous grin.

Olivia opened her mouth to answer but Sam stepped in, “This is Olivia...Winchester. Apparently we have a sister we never knew about.”

The air suddenly became tense. An awkward silence followed the tension. If anything, Olivia wanted to hide under the bed back in the motel room, but there was nowhere to run without either being caught by Sam or the stranger named Crowley.   
Crowley glanced back at Sam. “Good luck with your brother. What is it you humans say? Armed and dangerous?”

He disappeared into thin air, leaving Sam and Olivia to their own already awkward thoughts. Sam suddenly became concerned not only for his brother’s life, but for Olivia’s. Should he allow her to accompany him after what Crowley had just said?

He sat in the Impala unsure of what to say. On one hand, she’d be a great distraction if it was needed, but on the other, she could get hurt. Traumatizing the poor girl would be the least of his priorities, especially since she’s never really seen the core of supernatural elements. Sure, she’d seen Castiel in all his glory, and she’d just met Crowley, but a demonic brother? That was a sure fire way to send her straight back home.

“Look, Olivia, I...I know you want to help but -” Sam started, but she cut him off.

“But what? Am I not good enough? You don’t think I could do it?” She quickly started jumping to every conclusion in the book and confronted him. “You think Dean is too dangerous for me. Admit it.”

Sam sat in silence.

“You know what? I...I’m walking back to the bunker”, she pushed the door open angrily. “You better hope I don’t have to drag you out of that place.”

“Olivia wait!”, Sam tried to stop her. “You are not walking back to that bunker by yourself. You have no idea what’s out there and what knows you have connections with us as Winchesters. It’s too dangerous for you to be alone anywhere.”

Olivia gave him a fierce look. She may have been a lady, but she could give a man-to-man talk if she needed to. “I have walked the streets of some of the most dangerous places in this country. Don’t you dare tell me what I can and cannot face. I’m walking to that bunker whether you like it or not Sam Winchester. And that’s final!”

She grabbed her bags and walked off down the side of the road, leaving Sam to worry and wonder.


	4. Two Brothers And A Sister - Chapter 4

**Summary for the Chapter:**

> Will Olivia's greatest fears overcome her? Meeting Dean face to face will answer that.

Olivia shivered in the chill of the afternoon air. She practically ignored the worried phone calls from Sam and attempted to find her way back home, but unfortunately all it did was get her lost. Right in the middle of nowhere. That little inkling of Winchester pride kept telling her that she’d eventually make it home.

The familiar woosh of wings resounded behind her and she turned to face Cas. “Did Sam send you?”, she grumbled under her breath.

In a rather sassy tone, Cas answered, “Actually yes. He knew you’d get lost so he asked me to make sure you were safe.”

She texted Sam, Thanks for sending the angel but really? 

There was no response, but she imagined he was smirking at his phone.

Before Olivia could protest, Cas firmly grabbed her arm and landed in the bunker. But in her bedroom. 

“Um...Cas, why did you bring me to the bedroom? You usually bring me to the library or the kitchen”, she grumbled again, but a little louder this time.

Cas huffed and growled, “You really do act like a Winchester. Sam told me to bring you down here because he…” Cas stopped in his tracks. Should he tell Olivia? It might scare her, but she had every right to know. She even offered to be Sam’s support. “...Dean...is here...in the bunker. In the dungeon.”

Olivia could have sworn her heart stopped beating. Her brother was here. Well, technically he was her brother but in demon form. It would have been understatement to say she was terrified. Weeks ago when she first arrived, she was hoping for a warm welcome and perhaps some ice cream, but this? Having to face Dean Winchester as a demon? Part of her wanted to run. Part of her wanted to stay; but she entertained the latter.

Cas noticed the determined look in her eyes and scolded her. “Sam has also instructed you not to go down there. It is far too dangerous. That man in there is not Dean Winchester. Do I make myself clear?”

Olivia gulped and nodded silently, turning to her desk to flip through a magazine mindlessly. Sam knocked on the door a while later.

“Hey Liv…” Liv? Did Sam just give his little sister a nickname? “Cas and I are going out to do some research. Please stay out of the dungeon okay? You’ll be just fine.”

She nodded. “Eh if anything happens, I can just shoot my brother. After all, I don’t think it’s illegal to shoot a demon.”

“That’s my girl”, Sam chuckled and left, leaving the door cracked a little to let some light in.

Fifteen very long minutes passed before Olivia decided it was time to go to the kitchen. Hunger settled in and there was a very big need for lasagna. It was a little scary to say the least to walk down the hall, knowing that just beneath her feet, an angry demon was probably trying to get loose.

One step in front of the other...one step in front of the other...just breathe...she told herself. Suddenly, the lights in the bunker shut off. One by one, they went out. Olivia was left in the dark. One single light flashed back on, but it was a dark red. She could barely see an inch in front of her. Sweat drops began to form on her forehead; she was starting to be a nervous wreck. 

She turned the corner only to see a tall, menacing man approaching her. 

“Sam?! Please tell me that’s you!”, she squeaked. Only silence.

The man came closer until he had her cornered. “Sam’s not here sweetheart.” The man growled and his eyes flashed black and Olivia immediately recognized who it was. 

“Dean…” she whimpered.

“Dean’s not here either”, he pushed closer until she was practically pinned against the wall. 

The lights quickly flicked on and Olivia stood there face to face with her eldest brother.


	5. Two Brothers And A Sister - Chapter 5

**Summary for the Chapter:**

> Continuation of the meeting with Dean for the first time.
> 
> Does Olivia handle it in a good way?

Olivia stood under the tremendous strength of the eldest Winchester. All time seemed to stand still until she heard a familiar voice calling for her.

“Olivia?! Why are the lights…” The reprimand was cut short when Sam found her with Dean. Sam ran towards the demonic brother and swung his fist to punch but Dean threw him to the ground with very little effort, if any at all. 

Sam motioned for Olivia to run when Dean grabbed her by the arm. She let out a small scream but was let loose when Cas appeared behind Dean, restraining him from hurting anyone any further. Olivia looked into Dean’s eyes and saw nothing but pure evil. Pure negative, vile intent. His eyes flashed black again as he growled trying to pounce on her again. 

As Cas struggled to drag Dean away back to the dungeon, Sam stood to see a very shaken Olivia. Her mouth was agape, no words forming. There were no words for what just happened. She’d witnessed street fights, the occasional scuffle at college, but this? She had just had a very close encounter with a very real demon.

Sam, knowing she was at the point of tears, reached out to her and gently held her head against his chest. 

Her voice cracked as a tear ran down her face. “I’m scared Sammy.”

“I know sis. I know”, he consoled the best he could. His heart broke when her tears began to soak the blue flannel that he was wearing. “Come on, let’s get you out of here.”

Once you put together a few things, Sam took you to a motel to rest. He pulled up in the parking lot, unsure whether to leave you here or not. He decided against it seeing how much it really hurt you to see Dean like that, especially for the very first time, She didn’t get to see the piercing hazel eyes that Sam was used to. She didn’t get to laugh at his corny jokes or have Netflix binges. Honestly, he wouldn’t blame her if she wanted to leave town.

He turned around to see her half-asleep in the back of the car he’d been driving. 

“Come on Liv, I’ll help you get settled in”, he said in a soothing tone.

“You...you’re not gonna leave me here are you?”, she answered. Her eyes were bulging out of her head; the poor girl was terrified.

Sam sighed and shook his head. “Of course not. You want something to eat while it’s still decent out?”

She rejected the offer. The whole ordeal made her nauseous, which made the mention of food less and less appetizing.   
Later that night, Olivia tossed and turned in her sleep. In a dream, she found herself in the bunker with the lights dimmed down to that dark red. She could hear Dean’s voice echoing through the halls. She kept running around in circles trying to get away from the voice, but it was constantly behind her as if he was right there. The voice kept saying, “I’ll always find you. You can’t run, and you can’t hide. We demons always know where to look.”

She tripped and found herself falling until she hit the dungeon floor. After moving the hair out of her face, she looked up and saw Cas and Sam chained to the wall. Their faces were marred and bloody, and they were barely able to call out for her. Dean’s voice again sounded, “You can’t save them.”

In waking life, Sam grimaced, realizing that Olivia was having a nightmare. Tears started running down her face and she screamed loud enough that she woke herself up. 

Sam was right there beside of her. “Hey hey, it’s okay. It was just a dream. I’m here.” He rocked her back and forth as good as he knew how. 

Olivia whimpered, “He hurt you and Cas.”

“He’s not gonna hurt us sis. Calm down”, he rubbed her back up and down. His heart shattered thinking of what that did to her mind. All she wanted was to reunite with her brothers.


	6. Two Brothers And A Sister - Chapter 6

**Summary for the Chapter:**

> Olivia is still having a rough time with the fact that her eldest brother isn't himself. Castiel comes to her aid, and something miraculous happens.

The next day, Sam had no choice but to go back to the bunker. He had to confront the evil plague that was tormenting Dean. It took a while to talk Olivia into stepping back into that place, but she knew she had to go eventually. 

The conversation in the car was tense on the way.

“Liv, it’s going to be fine. Dean is locked away in the dungeon”, Sam sighed.

Olivia was having none of it. She crossed her arms in defense. “That seemed to help when you left me there alone.”

She had a point, but Sam countered. “Cas is keeping watch this time. We will not let him anywhere near you until he is human again.”

The rest of the ride was silent.

It was nearly sundown when they arrived back. The air was chilly but it was also dark, but not due to obvious reasons. It felt dark. The average joe wouldn’t have felt it, but then again, the average joe wouldn’t have a demon for a brother in the dungeon of a bunker. Once inside, Olivia scurried to her room where she knew she was safe. She cooped herself up in there reading and scrolling through her phone until it was time for her routine hot chocolate. She found that it helped her relax and sleep, but under current circumstances, that probably wasn’t going to be the case tonight. 

Olivia was hesitant to go in the hall to say the least. She breathed a sigh of relief when she made it to the kitchen. Grabbing a mug from the cabinet, her intention was to make the hot chocolate in peace. Unfortunately Cas appeared unexpectedly and caused her to throw the mug at him instinctively. The mug shattered on the kitchen floor.

Olivia mumbled as she swept it up, “Broken into tiny little pieces...just like my freaking life.” She shrieked when a piece of the glass pricked her finger. “Just my luck!”

Cas knelt down to her level, without a word, and healed her finger. He was unsure what to say, but Sam had told him to check on her while he confronted Dean. 

“Why are you doing this Cas?”, she asked, feeling ashamed of her outburst.

“Because I’m here to help. Dean...the real Dean...needs you to stay strong for him.” He replied calmly. The angel had a way with words. But as soothing as they may be, it still didn’t relieve the heartache deep inside Olivia’s gut. Her whole world was turned upside down. 

Suddenly the surroundings of the kitchen disappeared and both of them were now in the library. Cas had teleported...and with a new mug of hot chocolate. He handed it to Olivia tenderly and watched her carefully. 

“You humans fascinate me”, he blurted.

Olivia nearly spewed her beverage and giggled for the first time in a while. “Why is that?”

Cas tilted his head in confusion.

“I’m glad my statement amused you”. He paused before continuing. “Somehow, humans find the strength in the oddest of places. You seem content with the warmth of that mug; almost like that of your brother Dean...when he holds a bottle of beer.”

The angel’s observation hit the ball out of the park. Olivia stared at the mug and reflected quietly before speaking. “You’re right. I do find comfort in the simplest of things.” Her smile quickly turned into a half. “Do you think Dean will like me?”

Cas sat beside of her and she could feel something strange radiating from him. It was warm but not uncomfortable, and it made her feel secure. “Don’t worry. It’s just my grace...if you focus hard enough, you’ll feel my left wing wrapping around you.” 

She leaned in and nestled under the weight of an invisible comfort. 

He answered her question as she did so. “I believe that Dean will have a special bond with you. Because you helped save him.”

Tears brimmed in her eyes and she whimpered, “But he’s still a demon…”

Little did she know that Sam was standing there smiling at the loving bond between she and the angel. “Dean is no longer a demon Liv. Thank you for helping us.”

Olivia stood solemnly. “Can I…?”

Sam nodded and followed as she made her way to Dean’s room. Her heart pounded hard and loud, but her nerves screamed louder.


	7. Two Brothers And A Sister - Chapter 7

**Summary for the Chapter:**

> Dean has a secret...and Sam is determined to find out where Olivia came from.

**Notes for the Chapter:**

> If the flashback in this chapter had a particular setting, I'd guess and say it's probably in the earlier seasons. Or around the time when Sam still had Sully.
> 
> I'd like to thank MeganLouise for helping me get this part of the story going

Most girls Olivia’s age were terrified of walking on the stage to graduate college. Maybe they had butterflies before going on a first date. Perhaps they had a case of nerves going to a doctor. But not many were nervous to meet their brother for the first time, especially after an encounter with the evil thing that overtook him. 

Followed by Sam and Cas, she cautiously knocked on Dean’s bedroom door. She was expecting an angry tone, but instead was a calm...almost too calm...response.

“Sammy I...I’m busy right now. Maybe later”, he said from the other side of the door.

Sam leaned his head on the door and said, “This is important. There’s someone you need to meet.”

The three of them heard some scuffling around and intense footsteps approaching the door. They stood back as the brooding form of Dean Winchester made his way out. 

His eyes were immediately drawn to Olivia. Suddenly memories flooded his mind. Memories of conversations he had with his father years ago. One specific moment came to mind and tears brimmed his eyes.

“Livvy?” He said as he walked up to her, but she stepped back nervously, half-expecting the demon to come back any second. 

The tension in the air was thick and dark. It would have been awkward but to Olivia, awkwardness comes after something like tripping down the stairs or being caught singing in the shower. Here she was, with her eldest brother, and she had no clue what to say. Who could blame her though? Who in their right mind would know what to say to a former demon? 

Dean saw the fear in her eyes and immediately understood. He tried to speak but she stormed off in a fit of tears. Cas went after her while Sam and Dean had a confrontation.

“Livvy? Where did that come from?”, Sam questioned. “What are you not telling me?”

“Sam I knew…” Dean grumbled, slightly raising his voice. “I knew we had a sister, but...I never told you.”

If there was ever a time that Dean Winchester wanted to run and hide, this was that moment. He never thought he’d ever see that little girl again. 

Sam crossed his arms in annoyance and paced the room, practically circling Dean. “Care to explain? Is this yet another one of those secrets that dad told you to keep from me? How many more secrets are you going to keep from me Dean? This is getting old real quick, and I for one am very, very sick of it.”

Dean stood with a powerful glance at Sam. “You don’t think I’m not sick of it either? I carried that secret for heaven knows how many years. I lost count after dad…” The mention of John sent the room into an angry silence. 

After several minutes of contemplation, Dean finally gave in and explained everything.

FLASHBACK TO YOUNG!DEAN AND SAM

Dean awoke to the sound of a car door outside of their motel room. He looked around but their dad was nowhere in sight; a peek out the window and he noticed that John was talking to a woman. The woman was holding a small girl who seemed to be taking to John very well, almost as if he was a familiar face. Maybe too familiar. Dean watched as the woman turned towards the window with the child in her arms. Upon closer inspection, the little girl had eyes just like John Winchester. 

While Sam was still sleeping, Dean slipped outside to speak to his father. “Dad can I talk to you?”

“Hold on Gracie my boy needs me”, he said before being pulled aside.

“Excuse me for butting into your personal life, but what else have you been doing besides hunting all this time? That little girl over there? She has your eyes, and don’t you dare try to lie your way out of this one.” Dean gave him a disappointed glare. 

John didn’t try to defend himself, but he was firm in his response. “Listen Dean, I know what you’re thinking. You think I’m foolin’ around with a bunch of women but I’m not. She happens to be a hunter and that...is...our daughter.”

Dean crossed his arms and asked, “How old is she? The kid I mean.”

“Three…” John grumbled hesitantly. 

“So you mean to tell me, three years ago you decided to have a one night fling? Instead of worrying about the safety of the entire world? Thanks dad. Now I know where we stand.”

John was not about to let this go without trying to talk some sense into Dean. “You act like you’ve never made a mistake before. You act like you’re perfect. I got news for you. You’re no angel, but if you ever met one, I’d be hard pressed to say he’d enjoy your company.”

Dean lightened up a bit and repented of what he’d said. “I’m sorry dad...I...can I at least meet my sister? In case I never see her again? I promise I will never tell Sam.”

John agreed and introduced him to Gracie and the child, whose name was Olivia. “Hi Livvy, I’m Dean.” He took hold of her little fingers gently. “I’m your big brother, and if we ever meet again, I’ll protect you from all the monsters under your bed.”

Little Olivia grinned and squealed.

END OF FLASHBACK

Dean sat quietly waiting on Sam’s response. It wasn’t easy to tell him what transpired that day but sooner or later, it had to come out. But Dean never thought it would happen this way.

Sam sighed and rubbed his eyes. “Look, I understand...sort of...why you didn’t want to tell me. But now we have a responsibility to keep her safe, and I think she’s scared of you.”

Meanwhile, Olivia curled up silently on her bed crying. Cas did everything he could to console her, but it would have to take her and Dean to have a proper meeting.


End file.
